organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-{2-Methyl-5-[(5-oxo-10,11-di­hydro-5H-dibenzo[a,d]cyclo­hepten-2-yl)amino]­phen­yl}benzamide

aInstitute of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 10 June 2010; accepted 22 June 2010; online 30 June 2010)

In the title compound, C29H24N2O2, the two aromatic rings of the tricyclic unit are oriented at a dihedral angle of 32.27 (8)°. In the crystal N—H⋯O hydrogen bonds link the mol­ecules into chains along the a axis. Further N—H⋯·O inter­actions link the chains.

Related literature

For palladium-catalysed amination reactions of aryl halides with anilines, see: Jensen et al. (2004[Jensen, T. A., Liang, X., Tanner, D. & Skjaerbaek, N. (2004). J. Org. Chem. 69, 4936-4947.]); Grasa et al. (2001[Grasa, G. A., Viciu, M. S., Huang, J. & Nolan, S. P. (2001). J. Org. Chem. 66, 7729-7737.]). For p38 MAP kinase inhibitors based on dibenzosuberones, see: Laufer et al. (2006[Laufer, S. A., Ahrens, G. M., Karcher, S. C., Hering, J. S. & Niess, R. (2006). J. Med. Chem. 49, 7912-7915.]).

[Scheme 1]

Experimental

Crystal data
  • C29H24N2O2

  • Mr = 432.50

  • Orthorhombic, P b c a

  • a = 8.5878 (6) Å

  • b = 17.0342 (12) Å

  • c = 30.669 (2) Å

  • V = 4486.4 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.50 × 0.13 × 0.06 mm

Data collection
  • Bruker SMART APEXIIdiffractometer

  • 54075 measured reflections

  • 5388 independent reflections

  • 3740 reflections with I > 2σ(I)

  • Rint = 0.069

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.119

  • S = 1.00

  • 5388 reflections

  • 301 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N17—H17⋯O16i 0.88 (2) 2.04 (2) 2.8934 (18) 163 (1)
N25—H25⋯O27ii 0.91 (2) 2.01 (2) 2.8566 (17) 156 (1)
Symmetry codes: (i) x+1, y, z; (ii) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

Recently we designed and synthesized a series of p38 MAP kinase inhibitors based on dibenzosuberones (Laufer et al. 2006). The title compound was synthesized in the course of our ongoing studies on dibenzo[a,d]cycloheptan-5-ones as potent p38 mitogen-activated protein (MAP) kinase inhibitors.

The structure of the title compound, at 173 (2) K has orthorhombic symmetry. In the molecule (Fig.1), rings A (C1—C4, C14, C15) and B (C6—C11) are, of course, planar and they are oriented at a dihedral angle of A/B = 32.27 (8)°. In the crystal structure N17—H17···O16 (2.89 (2) Å) forms a chain parallel to the a-axis and N25—H25···O27 (2.86 (2) Å) links two by the c-glide plane related chains together (Fig.2).

Related literature top

For palladium-catalysed amination reactions of aryl halides with anilines, see: Jensen et al. (2004); Grasa et al. (2001). For p38 MAP kinase inhibitors based on dibenzosuberones, see: Laufer et al. (2006).

Experimental top

For the preparation of the title compound a mixture of 500 mg (2.1 mmol) 2-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, 470 mg (2.1 mmol) N-(5-amino-2-methylphenyl)benzamide, 940 mg (8.4 mmol) KOtert-Bu, 90 mg (0.19 mmol) 2-(dicyclohexylphosphino)-2'-, 4'-, 6'-triisopropylbiphenyl and 20 mg (0.09 mmol) Pd(OAc)2 in 3 ml absolute tert-butanol and 7 ml absolute toluol was stirred for 3 h at 264 K (90 °C) under an atmosphere of argon. The mixture was diluted with water then extracted with ethyl acetate. The extracts were combined, washed with saturated saline solution, dried over Na2SO4 and then evaporated under reduced pressure. The residue was purified by flash chromatography (SiO2 60, n-hexane / ethyl acetate 7 + 3) (yield: 16.3%). Crystals of the title compound were obtained by slow evaporation of a acetone / ethyl acetate / diethyl ether solution at room temperature. IR (ATR): 3312, 1648, 1575, 1544, 1511, 1292, 1275, 1263, 1109, 763, 701, 689cm-1. 1H-NMR (DMSO-d6) d in ppm: 2.21 (s, 3H), 3.07 (s, 4H), 6.87-7.04 (m, 3H), 7.20-7.59 (m, 8H), 7.84 (d, J=7.8 Hz, 1H), 7.96-8.01 (m, 3H), 8.80 (s, 1H, NH), 9.83 (s, 1H, NH). 13C-NMR (DMSO-d6) d in ppm: 17.7, 34.4, 36.2, 112.9, 114.3, 118.0, 118.3, 126.8, 127.3, 127.5, 128.0 (x2), 128.8 (x2), 129.0, 130.5, 131.3, 131.9, 132.2, 133.8, 135.0, 137.3, 139.3, 139.4, 142.0, 145.8, 149.0, 165.7, 191.0. HRMS-ESI, m/z (C29H24N2O2): calcd, 432.1838 [M+H]+; found, 432.1860.

1H NMR (200 MHz) and 13C NMR (50 MHz) were recorded on a Bruker Advance 200. IR data were determined on a Perkin-Elmer Spectrum One spectrometer (ATR technique). HRMS (EI) (electron impact – high resolution mass spectroscopy) data were obtained from the department for mass spectrometry, Institute of Organic chemistry, Eberhard-Karls-University Tübingen.

Refinement top

Hydrogen atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.98–0.99 Å (sp3 C-atom). Hydrogen atoms attached to N17 and N25 were located in diff. Fourier maps and refined using the AFIX 4 constraint (N-H distance is free to refine) with Uiso(H) = 1.2Ueq(N). All H atoms attached to carbon atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq(C) of the parent atom).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of compound the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the packing diagram illustrating the hydrogen bonds. View along the b-axis.
N-{2-Methyl-5-[(5-oxo-10,11-dihydro-5H- dibenzo[a,d]cyclohepten-2-yl)amino]phenyl}benzamide top
Crystal data top
C29H24N2O2F(000) = 1824
Mr = 432.50Dx = 1.281 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 6479 reflections
a = 8.5878 (6) Åθ = 2.4–24.1°
b = 17.0342 (12) ŵ = 0.08 mm1
c = 30.669 (2) ÅT = 173 K
V = 4486.4 (5) Å3Plate, yellow
Z = 80.50 × 0.13 × 0.06 mm
Data collection top
Bruker SMART APEXII
diffractometer
3740 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.069
Graphite monochromatorθmax = 27.9°, θmin = 2.4°
CCD scanh = 1111
54075 measured reflectionsk = 2122
5388 independent reflectionsl = 4039
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0522P)2 + 1.6792P]
where P = (Fo2 + 2Fc2)/3
5388 reflections(Δ/σ)max = 0.002
301 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C29H24N2O2V = 4486.4 (5) Å3
Mr = 432.50Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 8.5878 (6) ŵ = 0.08 mm1
b = 17.0342 (12) ÅT = 173 K
c = 30.669 (2) Å0.50 × 0.13 × 0.06 mm
Data collection top
Bruker SMART APEXII
diffractometer
3740 reflections with I > 2σ(I)
54075 measured reflectionsRint = 0.069
5388 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.24 e Å3
5388 reflectionsΔρmin = 0.19 e Å3
301 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.56067 (17)0.43978 (9)0.43200 (5)0.0264 (3)
C20.42391 (17)0.45759 (10)0.40902 (5)0.0303 (4)
H20.42940.48100.38100.036*
C30.28200 (17)0.44081 (10)0.42747 (5)0.0294 (3)
H30.19050.45390.41170.035*
C40.26547 (17)0.40522 (9)0.46867 (5)0.0266 (3)
C50.10305 (18)0.39527 (9)0.48427 (5)0.0291 (3)
C60.05457 (17)0.35895 (9)0.52689 (5)0.0278 (3)
C70.08844 (18)0.38403 (10)0.54369 (5)0.0327 (4)
H70.14290.42520.52940.039*
C80.1525 (2)0.35043 (11)0.58062 (5)0.0382 (4)
H80.24910.36890.59170.046*
C90.0751 (2)0.28965 (11)0.60145 (6)0.0416 (4)
H90.11970.26520.62630.050*
C100.0673 (2)0.26490 (10)0.58569 (6)0.0375 (4)
H100.12080.22390.60040.045*
C110.13471 (18)0.29860 (9)0.54876 (5)0.0295 (3)
C120.29383 (19)0.27248 (9)0.53467 (6)0.0332 (4)
H12A0.28760.24890.50520.040*
H12B0.33290.23190.55500.040*
C130.40667 (18)0.34182 (10)0.53394 (5)0.0308 (4)
H13A0.37970.37830.55790.037*
H13B0.51360.32230.53930.037*
C140.40373 (17)0.38601 (9)0.49132 (5)0.0249 (3)
C150.54564 (17)0.40451 (9)0.47287 (5)0.0260 (3)
H150.63760.39270.48880.031*
O160.00360 (13)0.42043 (8)0.46106 (4)0.0426 (3)
N170.70774 (15)0.45536 (8)0.41644 (4)0.0314 (3)
H170.7877 (18)0.45103 (13)0.4342 (4)0.038*
C180.74679 (17)0.47550 (9)0.37302 (5)0.0272 (3)
C190.68395 (17)0.43432 (9)0.33809 (5)0.0266 (3)
H190.61490.39170.34330.032*
C200.72163 (16)0.45516 (9)0.29563 (5)0.0254 (3)
C210.82292 (18)0.51809 (9)0.28699 (5)0.0297 (3)
C220.89126 (19)0.55434 (10)0.32282 (6)0.0350 (4)
H220.96620.59440.31790.042*
C230.85449 (18)0.53435 (10)0.36533 (5)0.0332 (4)
H230.90270.56080.38900.040*
C240.8502 (2)0.54853 (11)0.24131 (6)0.0401 (4)
H24A0.90540.59880.24270.060*
H24B0.74990.55590.22660.060*
H24C0.91300.51060.22490.060*
N250.66532 (14)0.41082 (8)0.25969 (4)0.0283 (3)
H250.7321 (14)0.3984 (3)0.2380 (5)0.034*
C260.53364 (17)0.36762 (9)0.25892 (5)0.0277 (3)
O270.43664 (12)0.36770 (7)0.28857 (4)0.0352 (3)
C280.51003 (18)0.31897 (10)0.21871 (5)0.0301 (4)
C290.4196 (2)0.25209 (11)0.22279 (6)0.0466 (5)
H290.37470.23900.25010.056*
C300.3948 (3)0.20449 (13)0.18704 (7)0.0627 (6)
H300.33530.15780.19010.075*
C310.4558 (3)0.22431 (13)0.14716 (7)0.0577 (6)
H310.43800.19130.12270.069*
C320.5426 (2)0.29157 (13)0.14238 (6)0.0496 (5)
H320.58290.30550.11460.060*
C330.5709 (2)0.33890 (12)0.17818 (6)0.0385 (4)
H330.63210.38500.17510.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0229 (7)0.0303 (8)0.0260 (8)0.0015 (6)0.0023 (6)0.0063 (6)
C20.0257 (8)0.0420 (9)0.0232 (8)0.0040 (7)0.0026 (6)0.0007 (7)
C30.0229 (8)0.0403 (9)0.0248 (8)0.0057 (6)0.0060 (6)0.0025 (7)
C40.0232 (7)0.0314 (8)0.0252 (8)0.0016 (6)0.0037 (6)0.0038 (6)
C50.0239 (8)0.0335 (8)0.0300 (8)0.0000 (6)0.0058 (6)0.0047 (7)
C60.0235 (7)0.0324 (8)0.0274 (8)0.0059 (6)0.0030 (6)0.0078 (6)
C70.0257 (8)0.0392 (9)0.0330 (9)0.0041 (7)0.0041 (7)0.0088 (7)
C80.0281 (8)0.0500 (11)0.0364 (10)0.0085 (8)0.0030 (7)0.0108 (8)
C90.0409 (10)0.0458 (11)0.0380 (10)0.0154 (8)0.0058 (8)0.0030 (8)
C100.0412 (10)0.0314 (9)0.0397 (10)0.0072 (7)0.0003 (8)0.0008 (7)
C110.0302 (8)0.0267 (8)0.0315 (8)0.0049 (6)0.0016 (7)0.0057 (6)
C120.0348 (9)0.0298 (8)0.0350 (9)0.0036 (7)0.0006 (7)0.0012 (7)
C130.0258 (8)0.0375 (9)0.0292 (8)0.0037 (7)0.0034 (7)0.0034 (7)
C140.0249 (7)0.0251 (7)0.0248 (8)0.0020 (6)0.0034 (6)0.0048 (6)
C150.0224 (7)0.0307 (8)0.0249 (8)0.0038 (6)0.0073 (6)0.0044 (6)
O160.0218 (6)0.0675 (9)0.0384 (7)0.0022 (6)0.0066 (5)0.0083 (6)
N170.0207 (6)0.0500 (9)0.0235 (7)0.0001 (6)0.0050 (5)0.0013 (6)
C180.0203 (7)0.0350 (8)0.0263 (8)0.0023 (6)0.0020 (6)0.0018 (6)
C190.0193 (7)0.0315 (8)0.0292 (8)0.0014 (6)0.0010 (6)0.0007 (6)
C200.0183 (7)0.0313 (8)0.0266 (8)0.0007 (6)0.0017 (6)0.0035 (6)
C210.0250 (8)0.0324 (8)0.0317 (8)0.0010 (6)0.0027 (7)0.0006 (7)
C220.0298 (9)0.0342 (9)0.0411 (10)0.0095 (7)0.0014 (7)0.0031 (7)
C230.0272 (8)0.0388 (9)0.0336 (9)0.0039 (7)0.0041 (7)0.0094 (7)
C240.0409 (10)0.0405 (10)0.0390 (10)0.0062 (8)0.0048 (8)0.0061 (8)
N250.0202 (6)0.0398 (8)0.0248 (7)0.0032 (5)0.0022 (5)0.0048 (6)
C260.0211 (7)0.0364 (9)0.0255 (8)0.0003 (6)0.0022 (6)0.0008 (6)
O270.0225 (5)0.0576 (8)0.0253 (6)0.0072 (5)0.0001 (5)0.0021 (5)
C280.0229 (7)0.0383 (9)0.0291 (8)0.0008 (7)0.0061 (6)0.0029 (7)
C290.0565 (12)0.0457 (11)0.0377 (10)0.0158 (9)0.0097 (9)0.0012 (8)
C300.0861 (17)0.0457 (12)0.0562 (14)0.0244 (12)0.0216 (12)0.0030 (10)
C310.0736 (15)0.0564 (13)0.0431 (12)0.0011 (11)0.0194 (11)0.0191 (10)
C320.0470 (11)0.0682 (14)0.0337 (10)0.0006 (10)0.0015 (9)0.0120 (9)
C330.0311 (9)0.0524 (11)0.0320 (9)0.0058 (8)0.0004 (7)0.0061 (8)
Geometric parameters (Å, º) top
C1—N171.3760 (19)N17—H170.880 (19)
C1—C151.396 (2)C18—C231.384 (2)
C1—C21.403 (2)C18—C191.390 (2)
C2—C31.374 (2)C19—C201.388 (2)
C2—H20.9500C19—H190.9500
C3—C41.409 (2)C20—C211.406 (2)
C3—H30.9500C20—N251.4210 (19)
C4—C141.414 (2)C21—C221.390 (2)
C4—C51.484 (2)C21—C241.512 (2)
C5—O161.2366 (19)C22—C231.384 (2)
C5—C61.505 (2)C22—H220.9500
C6—C71.399 (2)C23—H230.9500
C6—C111.407 (2)C24—H24A0.9800
C7—C81.383 (2)C24—H24B0.9800
C7—H70.9500C24—H24C0.9800
C8—C91.386 (3)N25—C261.3494 (19)
C8—H80.9500N25—H250.905 (18)
C9—C101.381 (3)C26—O271.2334 (18)
C9—H90.9500C26—C281.499 (2)
C10—C111.395 (2)C28—C291.384 (2)
C10—H100.9500C28—C331.391 (2)
C11—C121.501 (2)C29—C301.380 (3)
C12—C131.528 (2)C29—H290.9500
C12—H12A0.9900C30—C311.373 (3)
C12—H12B0.9900C30—H300.9500
C13—C141.509 (2)C31—C321.374 (3)
C13—H13A0.9900C31—H310.9500
C13—H13B0.9900C32—C331.384 (2)
C14—C151.380 (2)C32—H320.9500
C15—H150.9500C33—H330.9500
N17—C181.415 (2)
N17—C1—C15118.63 (13)C1—N17—C18126.19 (13)
N17—C1—C2123.55 (14)C1—N17—H17118.98 (8)
C15—C1—C2117.82 (14)C18—N17—H17114.78 (8)
C3—C2—C1119.41 (15)C23—C18—C19119.58 (14)
C3—C2—H2120.3C23—C18—N17119.62 (14)
C1—C2—H2120.3C19—C18—N17120.73 (14)
C2—C3—C4123.25 (14)C20—C19—C18120.25 (14)
C2—C3—H3118.4C20—C19—H19119.9
C4—C3—H3118.4C18—C19—H19119.9
C3—C4—C14117.11 (14)C19—C20—C21121.08 (14)
C3—C4—C5115.65 (13)C19—C20—N25120.82 (14)
C14—C4—C5127.18 (14)C21—C20—N25118.02 (13)
O16—C5—C4118.09 (14)C22—C21—C20116.81 (14)
O16—C5—C6115.95 (14)C22—C21—C24120.97 (15)
C4—C5—C6125.93 (13)C20—C21—C24122.13 (14)
C7—C6—C11118.48 (15)C23—C22—C21122.61 (15)
C7—C6—C5115.94 (14)C23—C22—H22118.7
C11—C6—C5125.38 (14)C21—C22—H22118.7
C8—C7—C6121.63 (16)C22—C23—C18119.42 (15)
C8—C7—H7119.2C22—C23—H23120.3
C6—C7—H7119.2C18—C23—H23120.3
C7—C8—C9119.75 (16)C21—C24—H24A109.5
C7—C8—H8120.1C21—C24—H24B109.5
C9—C8—H8120.1H24A—C24—H24B109.5
C10—C9—C8119.40 (17)C21—C24—H24C109.5
C10—C9—H9120.3H24A—C24—H24C109.5
C8—C9—H9120.3H24B—C24—H24C109.5
C9—C10—C11121.72 (17)C26—N25—C20126.07 (13)
C9—C10—H10119.1C26—N25—H25113.04 (9)
C11—C10—H10119.1C20—N25—H25118.67 (8)
C10—C11—C6118.99 (15)O27—C26—N25123.53 (14)
C10—C11—C12119.30 (15)O27—C26—C28121.05 (14)
C6—C11—C12121.65 (14)N25—C26—C28115.42 (13)
C11—C12—C13110.64 (13)C29—C28—C33119.51 (16)
C11—C12—H12A109.5C29—C28—C26117.15 (15)
C13—C12—H12A109.5C33—C28—C26123.32 (15)
C11—C12—H12B109.5C30—C29—C28119.88 (19)
C13—C12—H12B109.5C30—C29—H29120.1
H12A—C12—H12B108.1C28—C29—H29120.1
C14—C13—C12112.82 (13)C31—C30—C29120.3 (2)
C14—C13—H13A109.0C31—C30—H30119.9
C12—C13—H13A109.0C29—C30—H30119.9
C14—C13—H13B109.0C30—C31—C32120.45 (18)
C12—C13—H13B109.0C30—C31—H31119.8
H13A—C13—H13B107.8C32—C31—H31119.8
C15—C14—C4119.15 (14)C31—C32—C33119.76 (19)
C15—C14—C13117.03 (13)C31—C32—H32120.1
C4—C14—C13123.73 (14)C33—C32—H32120.1
C14—C15—C1123.23 (14)C32—C33—C28120.05 (17)
C14—C15—H15118.4C32—C33—H33120.0
C1—C15—H15118.4C28—C33—H33120.0
N17—C1—C2—C3179.11 (15)N17—C1—C15—C14179.60 (14)
C15—C1—C2—C30.7 (2)C2—C1—C15—C140.5 (2)
C1—C2—C3—C40.8 (3)C15—C1—N17—C18166.23 (15)
C2—C3—C4—C140.4 (2)C2—C1—N17—C1813.9 (3)
C2—C3—C4—C5177.03 (15)C1—N17—C18—C23137.86 (17)
C3—C4—C5—O162.0 (2)C1—N17—C18—C1945.3 (2)
C14—C4—C5—O16175.13 (15)C23—C18—C19—C203.9 (2)
C3—C4—C5—C6179.85 (14)N17—C18—C19—C20179.24 (14)
C14—C4—C5—C63.0 (3)C18—C19—C20—C210.3 (2)
O16—C5—C6—C724.6 (2)C18—C19—C20—N25176.39 (14)
C4—C5—C6—C7153.62 (15)C19—C20—C21—C224.4 (2)
O16—C5—C6—C11150.24 (16)N25—C20—C21—C22172.33 (14)
C4—C5—C6—C1131.6 (2)C19—C20—C21—C24172.18 (15)
C11—C6—C7—C80.7 (2)N25—C20—C21—C2411.1 (2)
C5—C6—C7—C8174.43 (14)C20—C21—C22—C234.7 (2)
C6—C7—C8—C90.9 (2)C24—C21—C22—C23171.97 (16)
C7—C8—C9—C101.8 (3)C21—C22—C23—C180.7 (3)
C8—C9—C10—C111.1 (3)C19—C18—C23—C223.7 (2)
C9—C10—C11—C60.5 (2)N17—C18—C23—C22179.41 (15)
C9—C10—C11—C12176.51 (15)C19—C20—N25—C2626.7 (2)
C7—C6—C11—C101.4 (2)C21—C20—N25—C26156.54 (15)
C5—C6—C11—C10173.26 (14)C20—N25—C26—O277.6 (3)
C7—C6—C11—C12175.52 (14)C20—N25—C26—C28173.21 (14)
C5—C6—C11—C129.8 (2)O27—C26—C28—C2926.9 (2)
C10—C11—C12—C13121.01 (16)N25—C26—C28—C29153.85 (16)
C6—C11—C12—C1355.9 (2)O27—C26—C28—C33151.57 (17)
C11—C12—C13—C1486.65 (17)N25—C26—C28—C3327.7 (2)
C3—C4—C14—C151.6 (2)C33—C28—C29—C302.1 (3)
C5—C4—C14—C15175.47 (15)C26—C28—C29—C30179.38 (18)
C3—C4—C14—C13174.79 (14)C28—C29—C30—C311.8 (3)
C5—C4—C14—C138.1 (2)C29—C30—C31—C320.2 (4)
C12—C13—C14—C15133.61 (14)C30—C31—C32—C331.2 (3)
C12—C13—C14—C442.9 (2)C31—C32—C33—C280.9 (3)
C4—C14—C15—C11.8 (2)C29—C28—C33—C320.7 (3)
C13—C14—C15—C1174.91 (14)C26—C28—C33—C32179.17 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O16i0.88 (2)2.04 (2)2.8934 (18)163 (1)
N25—H25···O27ii0.91 (2)2.01 (2)2.8566 (17)156 (1)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC29H24N2O2
Mr432.50
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)173
a, b, c (Å)8.5878 (6), 17.0342 (12), 30.669 (2)
V3)4486.4 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.50 × 0.13 × 0.06
Data collection
DiffractometerBruker SMART APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
54075, 5388, 3740
Rint0.069
(sin θ/λ)max1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.119, 1.00
No. of reflections5388
No. of parameters301
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.19

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O16i0.880 (19)2.040 (19)2.8934 (18)163.08 (17)
N25—H25···O27ii0.905 (18)2.005 (17)2.8566 (17)156.3 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y, z+1/2.
 

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGrasa, G. A., Viciu, M. S., Huang, J. & Nolan, S. P. (2001). J. Org. Chem. 66, 7729–7737.  Web of Science CrossRef PubMed CAS Google Scholar
First citationJensen, T. A., Liang, X., Tanner, D. & Skjaerbaek, N. (2004). J. Org. Chem. 69, 4936–4947.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLaufer, S. A., Ahrens, G. M., Karcher, S. C., Hering, J. S. & Niess, R. (2006). J. Med. Chem. 49, 7912–7915.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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